N-bromobutanimide → HCID 77520043, compound

Participants

Reaction Steps

N-Bromosuccinimide (60.3 g, 338 mmol) was added to a solution of 4-Chloro-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine (100 g, 323 mmol) in CH2Cl2 (1 L). After 12 h 15 the reaction was quenched with saturated aqueous NaHCO3 (500 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (4×500 mL). The combined organic layers were filtered through silica gel and concentrated in vacuo. Purification by flash column chromatography (ethyl acetate/hexanes 1:99) afforded the title compound as a clear solid (89.5 g, 72%). MS: 388.8/390.8 (MH+); HPLC Rf: 9.84 min. (HPLC method 4).

Provenance & Evidence